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WO2011067192A3 - Copolymère dithiénobenzo-thiéno [3,2-b] thiophène et son utilisation en tant que polymère semi-conducteur haute performance traitable en solution - Google Patents

Copolymère dithiénobenzo-thiéno [3,2-b] thiophène et son utilisation en tant que polymère semi-conducteur haute performance traitable en solution Download PDF

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Publication number
WO2011067192A3
WO2011067192A3 PCT/EP2010/068365 EP2010068365W WO2011067192A3 WO 2011067192 A3 WO2011067192 A3 WO 2011067192A3 EP 2010068365 W EP2010068365 W EP 2010068365W WO 2011067192 A3 WO2011067192 A3 WO 2011067192A3
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WIPO (PCT)
Prior art keywords
group
haloalkyl
alkyl
alkyl group
divalent
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Ceased
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PCT/EP2010/068365
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English (en)
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WO2011067192A2 (fr
Inventor
Marcel Kastler
Silke Koehler
Klaus Muellen
Ralph Rieger
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BASF SE
Max Planck Gesellschaft zur Foerderung der Wissenschaften
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BASF SE
Max Planck Gesellschaft zur Foerderung der Wissenschaften
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Priority to KR1020127016964A priority Critical patent/KR101780083B1/ko
Priority to JP2012541429A priority patent/JP5774599B2/ja
Priority to CN201080054412.3A priority patent/CN102639591B/zh
Priority to US13/511,890 priority patent/US8389670B2/en
Priority to EP10785057.0A priority patent/EP2507286B1/fr
Publication of WO2011067192A2 publication Critical patent/WO2011067192A2/fr
Publication of WO2011067192A3 publication Critical patent/WO2011067192A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/151—Copolymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/12—Copolymers
    • C08G2261/124—Copolymers alternating
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3243—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/414—Stille reactions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/90—Applications
    • C08G2261/92—TFT applications
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Thin Film Transistor (AREA)
  • Electroluminescent Light Sources (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Paints Or Removers (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

La présente invention a pour objet des copolymères dithiénobenzo-thiéno [3,2-b] thiophène de la formule (I) dans laquelle : pi est un fragment monocyclique ou polycyclique facultativement substitué par 1 à 4 groupes Ra, Ra, à chaque occurrence, étant indépendamment l'hydrogène ou a) un halogène, b) -CN, c) -NO2, d) un oxo, e) -OH, f) =C(Rb)2; g) un groupe alkyle en C1 à C20, h) un groupe alcényle en C2 à C20, i) un groupe alcynyle en C2 à C20, j) un groupe alcoxy en C1 à C20, k) un groupe alkylthio en C1 à C20, l) un groupe haloalkyle en C1 à C20, m) un groupe -Y- cycloalkyle en C3 à C10, n) un groupe -Y- aryle en C6 à C14, o) un groupe -Y- cyclohétéroalkyle à 3 à 12 chaînons, ou p) un groupe -Y- hétéroaryle à 5 à 14 chaînons, chacun des groupes suivants : le groupe alkyle en C1 à C20, le groupe alcényle en C2 à C20, le groupe alcynyle en C2 à C20, le groupe cycloalkyle en C3 à C10, le groupe aryle ou haloaryle en C6 à C14, le groupe cyclohétéroalkyle à 3 à 12 chaînons, et le groupe hétéroaryle à 5 à 14 chaînons, étant facultativement substitué par 1 à 4 groupes Rb; Y, à chaque occurrence, étant indépendamment un groupe alkyle en C1 à C6 divalent, un groupe haloalkyle en C1 à C6 divalent, ou une liaison covalente; et R1, R2, R3, à chaque occurrence, étant indépendamment H, un halogène, CN, un groupe alkyle en C1 à C30, un groupe alcényle en C2 à C30, un groupe haloalkyle en C1 à C30, un groupe alcynyle en C2 à C30, un groupe alcoxy en C1 à C30, un groupe C(O)- alkyle en C1 à C20, un groupe C(O)-O alkyle en C1 à C20, un groupe Y- cycloalkyle en C3 à C10, un groupe -Y- cyclohétéroalkyle à 3 à 12 chaînons, chacun étant facultativement substitué par 1 à 5 substituants choisis parmi un halogène, -CN, un groupe alkyle en C1 à C6, un groupe alcoxy en C1 à C6, et un groupe haloalkyle en C1 à C6, -L-Ar1, -L-Ar1 -Ar1, -L-Ar1-R4, ou -L-Ar1-Ar1-R4 et Y, à chaque occurrence, étant indépendamment un groupe alkyle en C1 à C6 divalent, un groupe haloalkyle en C1 à C6 divalent, ou une liaison covalente; n = 0, 1, 2; et o = 1 à 1 000.
PCT/EP2010/068365 2009-12-02 2010-11-29 Copolymère dithiénobenzo-thiéno [3,2-b] thiophène et son utilisation en tant que polymère semi-conducteur haute performance traitable en solution Ceased WO2011067192A2 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
KR1020127016964A KR101780083B1 (ko) 2009-12-02 2010-11-29 디티에노벤조-티에노［3,2-ｂ］티오펜 공중합체 및 고성능 용액 공정 가능한 반도체 중합체로서 이의 용도
JP2012541429A JP5774599B2 (ja) 2009-12-02 2010-11-29 ジチエノベンゾ−チエノ［３，２−ｂ］チオフェン−コポリマーとその溶液加工可能な高機能性半導電性ポリマーとしての利用
CN201080054412.3A CN102639591B (zh) 2009-12-02 2010-11-29 二噻吩并苯并噻吩并[3,2-b]噻吩共聚物及其作为高性能可溶液加工半导体聚合物的用途
US13/511,890 US8389670B2 (en) 2009-12-02 2010-11-29 Dithienobenzo-thieno[3,2-B]thiophene-copolymer and its use as high performance solution processable semiconducting polymer
EP10785057.0A EP2507286B1 (fr) 2009-12-02 2010-11-29 Copolymère dithiénobenzo-thiéno [3,2-b] thiophène et son utilisation en tant que polymère semi-conducteur haute performance traitable en solution

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US26577809P 2009-12-02 2009-12-02
US61/265,778 2009-12-02

Publications (2)

Publication Number Publication Date
WO2011067192A2 WO2011067192A2 (fr) 2011-06-09
WO2011067192A3 true WO2011067192A3 (fr) 2011-09-15

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PCT/EP2010/068365 Ceased WO2011067192A2 (fr) 2009-12-02 2010-11-29 Copolymère dithiénobenzo-thiéno [3,2-b] thiophène et son utilisation en tant que polymère semi-conducteur haute performance traitable en solution

Country Status (6)

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US (1) US8389670B2 (fr)
EP (1) EP2507286B1 (fr)
JP (1) JP5774599B2 (fr)
KR (1) KR101780083B1 (fr)
CN (1) CN102639591B (fr)
WO (1) WO2011067192A2 (fr)

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US20120289672A1 (en) 2012-11-15
CN102639591B (zh) 2015-05-13
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EP2507286A2 (fr) 2012-10-10
JP5774599B2 (ja) 2015-09-09
CN102639591A (zh) 2012-08-15
US8389670B2 (en) 2013-03-05
WO2011067192A2 (fr) 2011-06-09
EP2507286B1 (fr) 2017-07-05
KR20120116427A (ko) 2012-10-22

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